entacapone

Trade name: comtan

Small moleculeapproved

Approved

Oct 19, 1999

Entacapone is a selective, reversible catechol-O-methyl transferase (COMT) inhibitor for the treatment of Parkinson's disease. It is a member of the class of nitrocatechols. When administered concomittantly with levodopa and a decarboxylase inhibitor (e.g., carbidopa), increased and more sustained plasma levodopa concentrations are reached as compared to the administration of levodopa and a decarboxylase inhibitor. The mechanism of action of entacapone is believed to be through its ability to inhibit COMT in peripheral tissues, altering the plasma pharmacokinetics of levodopa. When entacapone is given in conjunction with levodopa and an aromatic amino acid decarboxylase inhibitor, such as carbidopa, plasma levels of levodopa are greater and more sustained than after administration of levodopa and an aromatic amino acid decarboxylase inhibitor alone. It is believed that at a given frequency of levodopa administration, these more sustained plasma levels of levodopa result in more constant dopaminergic stimulation in the brain, leading to a greater reduction in the manifestations of parkinsonian syndrome. Entacapone is used as an adjunct to levodopa / carbidopa in the symptomatic treatment of patients with idiopathic Parkinson's Disease who experience the signs and symptoms of end-of-dose "wearing-off". — NCATS

Clinical trial activity

49 trials · 41 clinical orgs · 13 marketing orgs

Phase 1
22
Phase 2
15
Phase 3
6
Phase 4
12

Earliest trial started Apr 1, 1997 (NCT00262470)

Timeline

1990s

  1. Jan 1, 1997

    Earliest Phase 1 Sponsor(trial)

  2. Oct 19, 1999

    Earliest FDA Approval

  3. Oct 19, 1999

    Orion Corporation — NDA Secondary Org

  4. Dec 30, 1999

    Orion Corporation — First NDA Organization

  5. Dec 30, 1999

    Orion Corporation — NDA Organization

2000s

  1. Jan 1, 2003

    Earliest Phase 2 Sponsor(trial)

  2. Jan 1, 2004

    Earliest Phase 3 Sponsor(trial)

2010s

  1. May 10, 2012

    Sun Pharmaceuticals — Marketing Organization

  2. Aug 16, 2012

    Atlantide Pharmaceuticals — Marketing Organization

  3. Aug 16, 2012

    Wockhardt — Marketing Organization

  4. May 13, 2013

    Mylan — Marketing Organization

  5. May 13, 2013

    PHARMOBEDIENT — Marketing Organization

  6. Jun 19, 2015

    Aurobindo Pharma — Marketing Organization

  7. Jun 5, 2017

    Macleods Pharmaceuticals, Ltd — Marketing Organization

  8. Jun 5, 2017

    Neogen — Marketing Organization

  9. Aug 31, 2017

    Ajanta Pharma Ltd — Marketing Organization

  10. Oct 3, 2018

    Sunshine Lake Pharma Co., Ltd. — Marketing Organization

2020s

  1. Jan 4, 2022

    Alembic — Marketing Organization

  2. Jan 25, 2022

    Rising Pharmaceuticals — Marketing Organization

Indications

Approved for

Mechanism of action

Combination products

Approval history

  • approvedOct 19, 1999

Chemistry & pharmacology

Loading structure…

SMILES

CCN(CC)C(=O)C(\C#N)=C\C1=CC(O)=C(O)C(=C1)[N+]([O-])=O
Mol. weight
305.286 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

No

Sources

Also known as

  • 2-cyano-n,n-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide
  • comtan
  • comtan
  • comtan
  • comtan
  • comtan
  • comtess
  • comtess
  • comtess
  • comtess
  • (e)-2-cyano-3-(3,4-dihydroxy-5-nitro-phenyl)-n,n-diethyl-prop-2-enamide
  • (e)-alpha-cyano-n,n-diethyl-3,4-dihydroxy-5-nitrocinnamamide
  • (e)-alpha-cyano-n,n-diethyl-3,4-dihydroxy-5-nitrocinnamamide
  • entacapona
  • entacapona
  • entacapone
  • entacapone
  • entacapone
  • entacapone
  • entacapone
  • entacapone
  • entacapone
  • entacapone
  • entacapone
  • entacapone
  • entacapone
  • entacapone
  • entacaponum
  • entacaponum
  • entacom
  • levodopa / carbidopa / entacapone
  • n,n-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide
  • n,n-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide
  • novartis brand of entacapone
  • or 611
  • or-611
  • or-611
  • or-611
  • orion brand of entacapone

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT07151378Phase 3Sep 16, 2025University of Tuebingen
NCT06180720Phase 1Dec 20, 2023Qingdao University
NCT06236230Phase 4Nov 15, 2023Soochow University
NCT05976737Phase 1Aug 17, 2023Qingdao University
NCT04952194Phase 4Jan 1, 2022Zhejiang University
NCT04246437Phase 1Feb 1, 2020Vanderbilt University
NCT04006769Early Phase 1 (Phase 1)Jul 31, 2019Central South University
NCT02764125Phase 2Apr 1, 2016Orion Corporation
NCT02554734Phase 1Aug 1, 2015Clinical Research Services Turku, Orion Corporation
NCT02448914Phase 1May 1, 2015LobSor Pharmaceuticals AB, TFS Trial Form Support, Uppsala University
NCT02452606N/AMar 1, 2015University of Ulsan
NCT02349243Phase 1/Phase 2 (Phase 2)Jan 1, 2015National Institute of Biological Sciences, Beijing, People's Liberation Army of China, Xijing Hospital
NCT01468012Phase 2/Phase 3 (Phase 3)Jul 1, 2014Columbia University
NCT02058966Early Phase 1 (Phase 1)Jun 1, 2014Department of Veteran Affairs, Oregon Health and Science University
NCT01840423Phase 1May 1, 2013Orion Corporation, Parexel
NCT01688089Phase 1Sep 1, 2012Orion Corporation, Parexel
NCT02170376Phase 1Sep 1, 2011Bial
NCT01766258Phase 2May 1, 2011Orion Corporation, Paracelsus Elena Klinik Kassel
NCT01568073Phase 3Mar 1, 2011Bial
NCT01437293Phase 1Aug 1, 2010Columbia University, National Institute on Drug Abuse (NIDA)
Showing 20 of 49 trials
Page 1 / 3

Organizations

Research & Development (41)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
NovartisFor profit121242003
Orion CorporationFor profit121142002
BialFor profit4432005
Columbia UniversityAcademic/Hospital2222010
ParexelFor profit2012012
Qingdao UniversityAcademic/Hospital2212023
Uppsala UniversityAcademic/Hospital2122008
Vanderbilt UniversityAcademic/Hospital2121997
Cardiff UniversityAcademic/Hospital1012005
Central South UniversityAcademic/Hospital1112019
Cita NeuroPharmaceuticalsFor profit1012006
Clinical Research Services TurkuFor profit1012015
Department of DefenseGovernment1012010
Department of Veteran AffairsGovernment1012014
Impax LaboratoriesFor profit1112010
INC ResearchFor profit1012006
LobSor Pharmaceuticals ABFor profit1112015
Molecular NeuroImagingFor profit1112004
National Institute of Biological Sciences, BeijingGovernment1012015
National Institute of Neurological Disorders and Stroke (NINDS)Government1112007
41 organizations
Page 1 / 3

Marketing (19)

OrganizationOrg typeRelationshipDate
Ajanta Pharma LtdFor profitMKTGAug 31, 2017
AlembicFor profitMKTGJan 4, 2022
AlembicFor profitSYNJan 4, 2022
Atlantide PharmaceuticalsFor profitMKTGAug 16, 2012
Aurobindo PharmaFor profitMKTGJun 19, 2015
Macleods Pharmaceuticals, LtdFor profitMKTGJun 5, 2017
MylanFor profitMKTGMay 13, 2013
MylanFor profitSYNAug 13, 2020
NeogenFor profitMKTGJun 5, 2017
Orion CorporationFor profitNDADec 30, 1999
Orion CorporationFor profitNDA2Oct 19, 1999
PHARMOBEDIENTFor profitMKTGMay 13, 2013
Rising PharmaceuticalsFor profitMKTGJan 25, 2022
Sun PharmaceuticalsFor profitMKTGMay 10, 2012
Sun PharmaceuticalsFor profitSYNMay 10, 2012
Sunshine Lake Pharma Co., Ltd.For profitSYNOct 3, 2018
Sunshine Lake Pharma Co., Ltd.For profitMKTGOct 3, 2018
WockhardtFor profitMKTGAug 16, 2012
WockhardtFor profitSYNAug 16, 2012